臺灣博碩士論文加值系統

摘要
在鋰離子電池中，石墨陽極電極表面的催化特性導致非水系有機碳酸鹽溶劑/電解液的分解過量，促進了不可逆反應，並在SEI上形成緻密的離子絕緣產物，且增加了電池內部電阻阻抗，另外，SEI與電解液的反應以及電解液的分解產物（二次反應）引起了SEI的劣化，使得鋰離子電池的功率密度與能量密度下降。
本文的首要動機是，進行鋰離子電池中具功能化的苯二甲基亞胺基電解液添加劑的合成與開發以及電解液添加劑之結構闡述，並通過對新添加劑的分子軌道性質進行理論研究來推斷其可還原性並評估其電化學特性。以陽極表面高勢下以1.1M LiPF6 -（EC / PC / DEC（2：3：5 v / v））電解液，在半電池與全電池系統中使用MCMB負極與LiCoO2正極所形成優質的SEI與CEI的可還原能力。因此，成功地合成了吸電子最多的官能團氟（F）和腈（-C≡N）取代苯二甲酰亞胺（MI），作為鋰離子電池中的電解液添加劑結構(F-MI 2F-MI與CN-MI)。
第二個動機是研究顯著消除兩個電極的界面阻抗中的氟取代效應，由於減少了固液界面中LiF和Li2CO3的含量而提高了電池的性能。此研究表明，在雙馬來酰亞胺結構中氟取代的對稱設計（兩個氟取代）與非對稱設計（一個氟取代）之間，對稱設計有效地抑制了石墨表面上雙馬來酰亞胺中-C = C-的直接電化學還原，並根據偶極矩的高強度與碳酸亞乙酯反應。在循環伏安法電池測試中表明，由於添加了對稱氟取代修飾的雙馬來酰亞胺，因此取得了顯著改善。電池性能證明，通過對稱氟取代修飾的雙馬來酰亞胺能夠分別將陽極半電池的電容量和全電池在2 C時，C-rate的性能提高7％和164％。這些新穎的電解液添加劑不僅預防了在電解液與固體界面中不必要的生成反應，且還增強了固液界面在陰極電解液界面與兩電極表面中的離子擴散性與電化學反應的可逆性。最後通過電化學石英晶體微天平以及使用ATR模式對電解質中MI的影響進行了臨場傅里葉轉換紅外光光譜分析，並對所有電解液系統進行了電解液與固體界面所形成的動力學分析。
在第三種動機中，研究了氟取代和腈取代的效果比較，由於在較高的還原電動勢（相對於Li / Li +）下，SEI層所形成原因如下：1）取決於電壓的事先還原所產生的電解液成分； 2）取代基的電負性效應會引起偶極環狀碳酸溶劑中電荷-偶極相的強烈相互作用，以及在非水體系中不可避免的雜質與鹽類的分解產物（根據添加劑的高極性）； 3）在陰極表面化學吸附的添加劑分子，用於抑制高電壓下電解液的分解與共嵌入以及電解液的氧化。因此，在該電化學表徵中，具有CN-MI添加劑的MCMB陽極半電池在LiCoO2 / MCMB全電池研究中顯示出最低的阻抗具極高的可逆電容量，但性能卻不及F-MI。
通過掃描式電子顯微鏡、X光射線電子能譜及核磁共振試驗陽極電極的形態和固體與電解液中間相的化學組成，以瞭解添加劑對MCMB電極表面形態組成之影響。因此，研究結果表示，由於在石墨陽極電池性能上優異的鈍化SEI之形成，得氟-腈取代的苯二甲基亞胺添加劑為合適的添加劑。
關鍵字：鋰離子電池、MCMB陽極、LiCoO2陰極、固體-電解液相、馬來酰亞胺、偶極矩、立體配位、氟官能化、腈官能化、吸電子、電荷-偶極相互作用非水系電解質、電化學測試。

Abstract
In lithium ion battery, the catalytic nature of graphite anode electrode surface cause decomposition of non-aqueous organic carbonate solvents/electrolytes more than required, at the same time fostering irreversible reaction and formation of dense and ionic insulating products on SEI increases total cell impedance, in addition, the reaction of SEI with electrolytes and the decomposition products of electrolytes (secondary reaction) cause deterioration of SEI, ultimately decay of power density and energy density of lithium ion battery.
The first motivation of this thesis is, carry out synthesis and development of functionalized phenylenedimaleimide based electrolyte additives in lithium ion battery, i.e. structural elucidations of electrolyte additives, evaluation of its electrochemical features through theoretical study of molecular orbital nature of new additives to deduce prior reducible ability at higher potential on anode surface and formation of quality SEI and CEI as well using MCMB as negative and LiCoO2 positive electrodes in half and full cell battery system in the presence of 1.1M LiPF6-(EC/PC/DEC(2:3:5 v/v)) electrolyte. Therefore, the most electron withdrawing functional groups, fluorine (F) and nitrile (-C≡N) substitution phenylenedimaleimide (MI) was successfully synthesized as F-MI 2F-MI and CN-MI used as an electrolyte additives in lithium ion batteries
The second motivation is investigation of significantly eliminating effects of fluorosubstitution in the interface impedances of the two electrodes and improves the rate performance of batteries because of the reduced LiF and Li2CO3 content in a solid electrolyte interphase. This study indicates that, between the symmetric (two fluorosubstitutions) and asymmetric (one fluoro substitution) designs of fluorosubstitution in bismaleimide structures, the symmetric design effectively inhibits the direct electrochemical reduction of –C=C- in bismaleimide on a graphite surface and reacts with ethylene carbonate in accordance with the high strength of the dipole moment. Cyclic voltammetry and battery measurements indicate considerable improvements due to the addition of bismaleimide modified through symmetric fluorosubstitution. Battery performance demonstrated that the addition of bismaleimide modified through symmetric fluorosubstitution was able to increase the capacity for anode half-cells and c-rate performance for full cells at 2 C by 7% and 164%, respectively. These novel electrolyte additives not only prevented unnecessary compound formations in the solid electrolyte interphase but also enhanced the ionic diffusivity and reversibility of the electrochemical reaction in the solid electrolyte interphase, cathode electrolyte interphase, and two-electrode surfaces. A kinetic analysis of solid electrolyte interphase formation was also performed on all electrolyte systems through an electrochemical quartz crystal microbalance and ex situ Fourier-Transform Infrared Spectroscopy analysis of the effect of MI in an electrolyte using ATR mode.
In the third motivation, the comparative effects of fluoro and nitrile substitutions are investigated, which arise from the SEI layer formation at higher reduction potential vs Li/Li+ due to 1) voltage dependent prior reduction to electrolyte component; 2) strong charge-dipole interactions with dipolar cyclic carbonated solvents, with unavoidable impurities in non-aqueous systems and decomposition products of salt in accordance with high polarity of additives arise from electronegativity effect of substituents; 3) chemisorbed additive molecules on the surface of cathode, which is used to suppressing the decomposition and co-intercalation of electrolytes and electrolyte oxidation at high charging voltage. Thus, in this electrochemical characterizations, MCMB anode half-cell battery with CN‐MI additive showed, the lowest impedance growth and higher reversible capacity but less perform than F-MI in LiCoO2/MCMB full-cell study
The morphology of the anode electrode and chemical composition of the solid electrolyte interphase were examined through scanning electron microscopy, X-ray photoelectron spectroscopy, and nuclear magnetic resonance in order to understand the effects of additive on the morphology and composition of MCMB electrode surface. Therefore the result of the study show that fluoro and nitrile substituted phenylenedimaleimide additives are suitable additives due to its excellent passivating SEI formation on graphite anode based battery performance improvement endeavors.

Keywords: Lithium ion battery, MCMB anode, LiCoO2 cathode, Solid electrolyte interphase, Maleimide, Dipole moment, Stereoscopic coordination, Fluorofunctionalized, Nitrile functionalized, Electron withdrawing, Charge-dipole interaction, Non-aqueous electrolyte, Electrochemical test.

Table of Contents
摘要 i
Abstract iii
Acknowledgments vi
Table of Contents viii
List of Figures xii
List of schemes xvi
List of Tables xvii
List of Abbreviations and Symbols Used xviii
Chapter I Introduction 1
1.1 Background 1
1.2 Lithium Ion Battery Cell Components 9
1.2.1 Cathode Materials in Lithium Ion battery 10
1.2.2 Anode Materials in Lithium Ion Battery 13
1.2.3 Electrolytes in Lithium Ion Battery 17
1.2.3.1 Electrolyte Solvents in Lithium Ion Battery 19
1.2.4 Separator in Lithium Ion Battery 22
Chapter II Literature Review 24
2.1 Electrolyte Additives in Lithium Ion Battery 24
2.1.1 Cathode Protection Additives 25
2.1.2 Safety Protection Additives in Lithium-Ion Batteries 28
2.1.3 Additive to Lower the Flammability of the Liquid Electrolytes in Lithium Ion Battery 30
2.1.4 Electrolyte Additive to Safety Concern with Lithium Salts in Lithium Ion Battery 31
2.1.5 Solid Electrolyte Interphase (SEI) and Electrolyte Additives That Improve Its Formation 33
2.1.6 Reduction-Type Additive 39
2.1.7 Reaction-Type Additive 42
2.1.8 Maleimide Based Electrolyte Additives in Lithium Ion Battery 44
2.2. Functional Groups Effect on Maleimide Based Electrolyte Additives 47
2.2.1 Fluoro Functionalized Maleimide based Electrolyte Additives in Lithium Ion Battery 48
2.2.2 Nitrile Functionalized Maleimide based Electrolyte Additives in Lithium Ion Battery 50
2.3 Research Innovation 51
Chapter III Methodology 54
3.1 Research Design 54
3.2 Materials and Reagents 55
3.3 Equipment 56
3.4 Experimental Procedure 57
3.4.1 Synthesis of Functionalized Electrolyte Additives 57
3.4.1.1 Hydrogenation steps for synthesis of 4-Fluoro-ortho-phenylenedimaleimide (F-MI) 57
3.4.1.2 Hydrogenation steps for synthesis procedure of 4, 5-difluoro-ortho phenylenedimaleimide (2FMI) 59
3.4.1.3 Dehydration (cyclization) steps for synthesis of 4-cyano-ortho-phenylenedimaleimide (CN-MI) 60
3.4.2 Density Functional Theory (DFT) calculations 61
3.4.3 Electrolyte and Electrode Preparation 62
3.4.4 Electrochemical Measurements and Characterizations 63
3.4. 4.1 Electrochemical Measurements 63
3.4. 4.2 Cyclic voltammetry measurements 65
3.4.4.3 Electrochemical Impedance Spectroscopy (EIS) Analysis 67
3.4.4.4 Electrochemical quartz crystal microbalance (EQCM) 69
3.5 Analytical Spectroscopic and Electron Microscopic Characterization of SEI 71
3.5.1 Fourier-Transform Infrared Spectroscopy (FTIR) Analysis 71
3.5.2 Scanning Electron Microscopy (SEM) and Energy Dispersive Spectrometer (EDS) 74
3.5.3 X-ray Photoelectron Spectroscopy (XPS) 74
3.5.4 Nuclear Magnetic Resonance (NMR) Spectroscopy 76
Chapter IV Analytical Spectroscopic Characterization of Electrolyte Additives for Molecular Structure Elucidation 78
4.1 Structural Elucidation of 4-Fluoro-1, 2-Phenylenediamine and 4-Fluoro Phenylenedimaleimide (FMI) 78
4.2 Structural Elucidation of 4, 5-difluoro-phenylenediamine and 4, 5-difluoro-phenylenedimaleimide (2FMI) 82
4.3 Structural Elucidation of 4-Cyano-phenylenedimaleimide (CN-MI) 85
4.4 ATR-FTIR Spectra Analysis of Functionalized Phenylenemaleimide Based Electrolyte Additive Molecules 88
Chapter V Investigation of the Dipole Moment Effects of Fluorofunctionalized Electrolyte Additives in a Lithium Ion Battery 89
5.1 Introduction 89
5.2 Results and Discussion 91
5.2.1 Cyclic Voltammetry Analysis of Electrolytes 91
5.2.2 Battery Performance and EIS Analysis of MCMB Half Cells 94
5.2.3. Ex Situ Fourier-Transform Infrared Spectroscopy Analysis of the Effect of MI in an Electrolyte 96
5.2.4 SEM and XPS Analysis of the MCMB Surface 100
5.2.5 EQCM and NMR Analysis of SEI 103
5.2.6 EIS Analysis and c-Rate Measurements of a Full Cell 106
5.2.7 Proposed Reaction Mechanism of the SEI 107
5.3 Conclusion 108
Chapter VI Studies on Comparative Effects of Fluoro and Nitrile Functional Group Substitution Phenylenemaleimide Based Electrolyte Additives in Lithium Ion Battery 109
6.1 Introduction 109
6.2 Results and discussions 112
6.2.1 Cyclic Voltammetry Analysis of Substituent Induced Property of Electrolytes and MI Additives 112
6.2.2 Charge Discharge Characteristics of Li/MCMB Half-Cell with Additives 115
6.2.3 Cycle-Ability Analysis of Li/MCMB Half-Cell Using MI Additives 117
6.2.4 Analysis of Electrochemical Impedance Spectroscopy 119
6.2.5 Cell Performance of LiCoO2/MCMB Full Cell with Additives 120
6.2.6 Cycle-Ability Analysis of LiCoO2/MCMB Full Cell LIB with Additives 121
6.2.7 Rate Capability Analysis of LiCoO2/MCMB Full Cell 123
6.2.8 Electrochemical Impedance Spectroscopy Studies on LiCoO2/MCMB Full Cell 124
6.2.9 SEM analysis of MCMB surface 126
6.2.10 Surface composition analysis of the MCMB electrodes 127
6.3 Conclusions 130
Chapter VII Conclusion and Future work 131
References 134
Appendix 163
CURRICULUM VITAE 167

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